A clear turquoise sea, a small island with dense green foliage, and a clear blue sky.

Villas in Portland

Compare and save

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Top Cities in Portland

A beach with clear turquoise water, a rocky coastline, and a small structure on a cliff.
VillasVillas

Port Antonio

Port Antonio
A tropical beach with palm trees and a clear blue sky.
VillasVillas

Buff Bay

Buff Bay

Our top choices for Portland villas

A wooden deck with a table and chairs, surrounded by lush greenery and a view of distant mountains.

1. Reggae Legends Estate

Reggae Legends Estate
3.5 star property
Jack's Hill
9.8 out of 10, Exceptional, (6 reviews)
"A really amazing find! Stunning location with fantastic views. Quiet and relaxing. The cabin was a great experience and we were so well looked after by Anne-Marie."
United Kingdom
Nicola
The price is AED 517
AED 598 total
includes taxes & fees
14 Oct - 15 Oct
Reggae Legends Estate
A balcony with a red railing, a black chair, and a potted plant.

2. Kai's Place @ Tim Pappies 3rd Floor luxury villa

Kai's Place @ Tim Pappies 3rd Floor luxury villa
Port Antonio
10.0 out of 10, Exceptional, (3 reviews)
"Even though there were some mixup with the booking thru VRBO, and spotty gps, which caused some initial inconveniences. The beautiful settings, comfortable room and Sangela's attentiveness, made it a very pleasant stay!"
Canada
rohan k r.
Kai's Place @ Tim Pappies 3rd Floor luxury villa
A row of single-story houses with tiled roofs, a well-maintained garden, and a clear sky.

3. Sunrise Villa On The Beach

Sunrise Villa On The Beach
3.0 star property
Portmore
8.6 out of 10, Excellent, (10 reviews)
"Quite environment great staff would definitely come again"
United States
Samoya
Sunrise Villa On The Beach
A large, yellow building with a swimming pool and multiple balconies, surrounded by lush greenery and a view of the ocean.

4. The Palms at Oracabessa *Luxury Vacation Rental* Fully Staffed

The Palms at Oracabessa *Luxury Vacation Rental* Fully Staffed
Oracabessa
8.8 out of 10, Excellent, (26 reviews)
"We really enjoyed our stay. The villa is modern and beautiful. The views from the balconies were amazing. The staff were attentive but discreet, Chef Shavon was very accommodating, one of our party was lactose intolerant with other intolerances and he at no point forgot that.We ate the mangoes which had fallen from the trees and they were so sweet and juicy.Our stay was short but memorable - it was very relaxing."
United States
M. S.
The price is AED 5,521
AED 6,307 total
includes taxes & fees
13 Oct - 14 Oct
The Palms at Oracabessa *Luxury Vacation Rental* Fully Staffed
A covered outdoor area with a wooden bench and table, surrounded by a railing and lush greenery.

5. Casa Victoria Golf Retreat

Casa Victoria Golf Retreat
4.0 star property
Kingston
9.8 out of 10, Exceptional, (72 reviews)
"Our stay was very comfortable and relaxing,we didn't stay in but it had all the nesscessary things that we were looking for. I would recommend it to anyone who are travelling with their family to stay there.lovely place,!!"
Canada
Desmond
Casa Victoria Golf Retreat
A two-story building with a tiled entrance and a gated driveway.

6. Windbreak Villa

Windbreak Villa
3.5 star property
Buff Bay
10.0 out of 10, Exceptional, (1 review)
The price is AED 308
AED 358 total
includes taxes & fees
13 Oct - 14 Oct
Windbreak Villa
A balcony with a view of the ocean, a lounge chair, and two drinks on a table.

7. Purevibe 2 BR/2 BA, Ocean View Villa, Private Rooftop, Near Port Antonio

Purevibe 2 BR/2 BA, Ocean View Villa, Private Rooftop, Near Port Antonio
Snow District
10.0 out of 10, Exceptional, (3 reviews)
"Randy's place is clean and is exactly as seen online. Must come back here"
Canada
Max L.
The price is AED 826
AED 1,057 total
includes taxes & fees
16 Oct - 17 Oct
Purevibe 2 BR/2 BA, Ocean View Villa, Private Rooftop, Near Port Antonio
A covered outdoor area with a pool, surrounded by potted plants and outdoor furniture.

8. Spicy Hill Villa, One Of Jamaica's Best-Kept Secrets.

Spicy Hill Villa, One Of Jamaica's Best-Kept Secrets.
Port Antonio
9.4 out of 10, Exceptional, (15 reviews)
"The staff made the visit memorable. "
United States
Eric
The price is AED 3,306
AED 3,776 total
includes taxes & fees
9 Nov - 10 Nov
Spicy Hill Villa, One Of Jamaica's Best-Kept Secrets.
A clear blue pool surrounded by a white fence with palm trees and a 'NO DIVING' sign.

9. The Country Club Villa I

The Country Club Villa I
3.5 star property
Kingston
9.0 out of 10, Wonderful, (10 reviews)
"The management team was awesome, the AC didn’t work in the main room on the first night but Ms Vicki made sure that I didn’t go a second night without it."
United States
Anonymous traveler
The Country Club Villa I
A balcony with a clear view of the sea and a distant island.

10. Heaven Villa - We are not on the water, we are above!

Heaven Villa - We are not on the water, we are above!
Port Antonio
9.2 out of 10, Wonderful, (13 reviews)
"the views of the surrounding area "
United States
Christopher
Heaven Villa - We are not on the water, we are above!
A pool with a clear view of the sea and a distant cityscape during sunset.

11. C-Vue Villa (Pool AC Gated Sea Front )

C-Vue Villa (Pool AC Gated Sea Front )
Portmore
9.6 out of 10, Exceptional, (12 reviews)
"This property exceeded all expectations and we all had a wonderful and comfortable stay. If you are looking for somewhere to relax with the sound of the waves and waking up to the sun rising over the ocean this is it. Beautifully maintained, secure property and grounds, great communication from the host, before, during and after our stay, thank you Michael we will be back"
United Kingdom
Naomi A.
C-Vue Villa (Pool AC Gated Sea Front )
A swimming pool with a white fence, surrounded by buildings with red roofs and palm trees.

12. The Oasis Golf Retreat

The Oasis Golf Retreat
3.0 star property
Kingston
9.6 out of 10, Exceptional, (4 reviews)
"IT WAS WONDERFUL.. VERY CLEAN , QUIET..JUST LOVELY.. "
United States
MARLON
The Oasis Golf Retreat
A waterfront property with a house, a dock, and clear blue water.

13. LillyBelleMar,San San Port Antonio,with pristine views and world class amenities

LillyBelleMar,San San Port Antonio,with pristine views and world class amenities
Fairy Hill
10.0 out of 10, Exceptional, (1 review)
"We had the best time during our stay. It was such a pleasure being back in this home and the staff are truly amazing "
United States
Olivia S.
LillyBelleMar,San San Port Antonio,with pristine views and world class amenities
A covered outdoor seating area with a sofa and a table, surrounded by arches and a railing, overlooking a scenic view.

14. 2 Villas in Jamaica-22 guests-Fully staffed

2 Villas in Jamaica-22 guests-Fully staffed
Galina
10.0 out of 10, Exceptional, (1 review)
"Really appreciated the kindness of the staff and great cooking! Chef Keamary was great at making what we wanted and surprising us with delicious Jamaican cooking. Housekeepers Cavisha and Simone were unobtrusive and got everything tidy. Spacious rooms and nice bathrooms, too. "
United States
Allison W.
2 Villas in Jamaica-22 guests-Fully staffed
A residential area with a house, lush greenery, and a clear sky.

15. Tapioca Village Retreat

Tapioca Village Retreat
3.0 star property
Castleton
6.0 out of 10, (2 reviews)
"There is so much nature and friendliness! "
United States
Günter
The price is AED 250
AED 291 total
includes taxes & fees
22 Oct - 23 Oct
Tapioca Village Retreat
A modern kitchen with grey cabinets, stainless steel appliances, and a window with grey curtains.

16. Carter's Nest Villa

Carter's Nest Villa
3.5 star property
New Kingston
The price is AED 661
AED 2,187 total
includes taxes & fees
13 Oct - 14 Oct
Carter's Nest Villa
A balcony with two cushioned chairs and a table, overlooking a beach and ocean.

17. Private Oceanside Luxury Villa Near Ocho Rios, Chef & Staff Included

Private Oceanside Luxury Villa Near Ocho Rios, Chef & Staff Included
Stony Hill
9.0 out of 10, Wonderful, (2 reviews)
"Unbelievable a great place to vacation with friends and family. Staff very accommodating and easy to communicate with. This is my new vacation spot in Jamaica!!"
United States
Dawn S.
Private Oceanside Luxury Villa Near Ocho Rios, Chef & Staff Included
A two-story house with a well-maintained lawn and vibrant red flowers in the front yard.

18. 4-bedroom villa in peaceful Portmore with AC

4-bedroom villa in peaceful Portmore with AC
Greater Portmore
4-bedroom villa in peaceful Portmore with AC
deck looking out at sea

19. "Sought-After" Secluded Private Beach Cove,14 Rooms, Retreat Center Destination

"Sought-After" Secluded Private Beach Cove,14 Rooms, Retreat Center Destination
St Mary
10.0 out of 10, Exceptional, (1 review)
"Strawberry Fields Together is a hidden gem! We stayed for three days with a large group from the United States because our previous travel plans fell through as many of the resorts were under renovation due to Hurricane Melissa and, now that we experienced the real Jamaica, I don't think we will ever go back. First of all, the grounds are what I imagine paradise looking like. Beautiful beaches, gardens, views, etc. Second, the accommodations are unique and charming. While they may lack some of...
United States
Mike S.
The price is AED 22,038
AED 29,645 total
includes taxes & fees
16 Oct - 17 Oct
"Sought-After" Secluded Private Beach Cove,14 Rooms, Retreat Center Destination
Pool

20. Timeless - Lovely beach cottage. Private pool, ocean view, beach access. R &R !

Timeless - Lovely beach cottage. Private pool, ocean view, beach access. R &R !
Kingston
9.6 out of 10, Exceptional, (4 reviews)
"Excellent stay. Very thorough check in info and attentive communication from the host. Beautiful home in a beautiful location. Can't wait to return."
United States
Amahra S.
Timeless - Lovely beach cottage. Private pool, ocean view, beach access. R &R !
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Portland Hotel Reviews

Match Resort Hotel

Match Resort Hotel

8/10 Good
"It was close enough to Port Antonio without being in town"
Laurene 5-night trip
Posted 2 days ago
Match Resort Hotel

Frequently asked questions

Why book your villa in Portland with Expedia?
Expedia makes it a cinch to find your ideal villa in Portland. Vacationing with the kids? Use our helpful filters to look for stays with amenities like free WiFi. If you have a budget in mind, select how much you want to spend and the star rating of the property. We'll help you find the perfect pad that gels with your style and taste.
How can I find cheap villas in Portland?
With Expedia's handy filter tool, booking cheap villas in Portland is easy. To discover options that are easy on the wallet, narrow down your search by amenities, budget and star rating.

Explore a world of travel with Expedia